When the calendar turns to September, Napa Valley begins its quiet transformation. The days are still warm, but the evenings bring a cool breeze. Vineyards glow golden as leaves start to change, and the hum of harvest fills the air. It’s a time of year when the valley feels alive, yet never hurried. For travelers, this shift makes fall the perfect moment to step off the beaten path and explore wine country at a slower pace.
One of the best things to do in Napa Valley during this season is to set out on a scenic drive. Whether you’re tracing iconic highways, winding through wooded backroads, or skirting the edges of tranquil lakes, these routes give you a front-row seat to the valley’s seasonal beauty. At the northern tip of Napa Valley, our Calistoga bed and breakfasts make the perfect starting point, or the perfect retreat, after a day on the road.
Let’s take a look at the best scenic drives in Napa Valley, each one offering its own blend of charm, color, and fall magic.
The Silverado Trail: Napa Valley’s Serene Side
Trimmed with shady oaks and world-class vineyards, the Silverado Trail is quintessential Napa Valley. Originally constructed in 1852 as the first permanent road linking Napa to Calistoga, this two-lane country road runs for about 29 miles as the quieter counterpart to the busier Highway 29.
In the fall, it becomes a ribbon of color. Vineyards glow amber and crimson, and the surrounding hillsides shift into warm hues. The road is dotted with so many wineries that you could spend a week here and still not visit them all. Along the way, you’ll pass names like Stag’s Leap Wine Cellars, Rutherford Hill, and Joseph Phelps, but even if you don’t stop, the sweeping views alone are worth the drive.
The stretch near Calistoga is particularly scenic, with gentle curves, less traffic, and a backdrop of Mount St. Helena. It’s also a favorite for cyclists, frequently named among the Top 5 Biking Trails Near Calistoga, CA. Whether you’re pedaling or cruising by car, this serene corridor is one of the best ways to take in Napa Valley’s beauty at a slower pace.
For those who want to venture higher, a detour onto Howell Mountain Road offers oak woodlands, elevated vineyard estates, and pull-offs with panoramic valley views.
Highway 29: The Classic Napa Valley Road Trip
No list of Napa Valley road trip routes would be complete without Highway 29, also known as St. Helena Highway. It’s the most iconic drive in the valley, linking the towns of Yountville, Oakville, Rutherford, St. Helena, and finally, Calistoga.
Yes, it’s busier than the Silverado Trail, but that’s part of its charm. In September and October, Highway 29 buzzes with the excitement of harvest. Vineyards brim with grapes ready to pick, and the air carries the earthy aroma of fermentation. The drive itself is lined with iconic stops, historic estates like Beringer Vineyards, and towns filled with tasting rooms, shops, and galleries.
Calistoga to Spring Mountain Loop: From Fossils to Forested Vistas
For a road trip that mixes natural history, hidden wineries, and sweeping views, begin in Calistoga and head west on Petrified Forest Road. Just a few minutes out of town, you’ll reach the Petrified Forest, where 3.4-million-year-old redwoods have been turned to stone. A short walk among the fossilized trees is a fascinating stop before the road winds upward.
From there, continue climbing through wooded hills as Petrified Forest Road crests over Spring Mountain. The drive is shaded and quiet, with towering trees giving way to occasional openings that reveal glimpses of the valley below. On the descent, Spring Mountain Road brings you into St. Helena, where boutique wineries tucked into the slopes offer intimate tastings far removed from the main highway buzz.
To complete the loop, head north on Highway 29 back to Calistoga. The combination of wooded ridges, artisanal wineries, and classic valley views makes this one of Napa’s most rewarding drives.
Lake Berryessa & Pope Valley: Off the Beaten Path
East of Napa Valley lies one of its most underrated drives. Head toward Lake Berryessa and Pope Valley, where rolling hills and oak woodlands stretch into quiet horizons.
Lake Berryessa offers sparkling water views, picnic areas, and plenty of scenic pull-offs where you can pause to take it all in. In late October, the contrast between golden vineyards, russet oak leaves, and blue lake waters is nothing short of spectacular. Pope Valley, meanwhile, is rural and charming with working ranches, stretches of road where you might not see another car for miles, and iconic tasting rooms like Pope Valley Winery, a historic stone cellar dating back to 1897.
Yountville to Rutherford Loop
If you’re short on time but still want a taste of Napa Valley’s fall beauty, this loop from Rutherford through Yountville is the perfect choice. Start in Rutherford and head east on Skellenger Lane until you reach the Silverado Trail. Turn south and enjoy the serene stretch of vineyards before cutting west on Yountville Cross Road into the heart of Yountville.
Here, you can slow down and explore the art of wine country with a stroll through the Yountville Art Walk, where sculptures line the pedestrian-friendly main street, or stop into boutiques and tasting rooms. Grab gourmet picnic provisions at Oakville Grocery before continuing north on Yount Mill Road. This peaceful byway threads through family-run vineyards and pastoral farmland, a striking contrast to the bustle of nearby Highway 29.
The road rejoins Highway 29, leading you back to Rutherford. End the loop with a meal at Rutherford Grill or return to Yountville for dinner at one of its acclaimed restaurants. This short but scenic route blends polished elegance with rustic charm, proving that small detours often yield the biggest rewards.
Seasonal Highlights: Fall in Napa Valley
What makes fall such a magical time for a Napa Valley road trip? For one, September marks the beginning of harvest season. Vineyards bustle with activity as grapes are picked, sorted, and crushed into the year’s vintages.
It’s also when the landscape starts shifting into fall colors. By mid-October, vines turn golden, hillsides deepen into rust tones, and the whole valley glows in soft light. Add in crisp mornings, soft evening light, and quieter roads, and you have the perfect recipe for a scenic drive.
Back to Calistoga: Relax After the Drive
After a day spent exploring the valley’s scenic routes, returning to Calistoga feels like coming home. Nestled at the northern end of Napa Valley, the town is perfectly positioned as a home base for your drives. You’re close to Highway 29 and Silverado Trail, yet just far enough removed to enjoy quiet evenings and starry skies.
The Craftsman Inn and Wine Way Inn are designed for exactly this kind of getaway. Picture yourself pulling back into town, parking the car, and stepping into a space where comfort and charm welcome you at every turn. Settle onto a garden patio with a glass of wine, reminisce about the day’s sights, and let the pace of Calistoga remind you why you came.
Because Napa Valley isn’t just about the tastings or the tours, sometimes, it’s about the simple joy of rolling down the windows, following the curves of the road, and letting the landscape unfold one vineyard at a time.
Book your stay and experience the most scenic drives in Napa Valley.